5-Chloro-2-cyanopyridine → (5-Chloropyridin-2-yl)methanamine

HRID 555782Notes

Reaction equation

HRID 555782 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=1>CCO.Cl.[Pd]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][NH2:9])=[N:6][CH:7]=1

Participants

5

Reactant 1

HCID 38339425-Chloro-2-cyanopyridine

Product 1

HCID 21069929(5-Chloropyridin-2-yl)methanamine

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

A mixture of 5-Chloro-2-cyanopyridine (1.5 g, 10.8 mmol) and 10% Pd/C (0.4 g) in EtOH (40 mL) and conc HCl (1.2 mL) is shaken under a H2-atmosphere (1 bar). After 2 h, the reaction mixture is filtered through Celite and carefully washed with THF. Concentration in vacuo and silica gel flash chromatography of the residue affords the title compound as a white solid; ES-MS: M+H=143.0: CtRet=3.33.

Workup

  1. filtrationthe reaction mixture is filtered through Celite
  2. washcarefully washed with THF
  3. concentrationConcentration in vacuo and silica gel flash chromatography of the residue

Sources & evidence

ORD record
ord-683d653ec5ac47bfa7458f9de4c51dcc
Source dataset
uspto-grants-2011_11
Patent number
US08053457B2

Reaction notes

Loading…